Photocatalytic aerobic oxidation of benzylic alcohols and concomitant hydrogen peroxide production

The photochemical oxidation of benzylic alcohols using N -hydroxyphthalimide (NHPI) catalyst, with Rose Bengal as a singlet oxygen photosensitizer, and the production of hydrogen peroxide (H 2 O 2 ) under metal-free conditions is presented. Computational and experimental investigations support 1 O 2...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2023-01, Vol.59 (8), p.19-193
Hauptverfasser: Bhattacharjee, Avik, LaVigne, Aireth R, Frazee, Serena M, Herrera, Tyler L, McCormick, Theresa M
Format: Artikel
Sprache:eng
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Zusammenfassung:The photochemical oxidation of benzylic alcohols using N -hydroxyphthalimide (NHPI) catalyst, with Rose Bengal as a singlet oxygen photosensitizer, and the production of hydrogen peroxide (H 2 O 2 ) under metal-free conditions is presented. Computational and experimental investigations support 1 O 2 as the oxidant that converts NHPI to the active radical intermediate phthalimide- N -oxyl (PINO). This is a green alternative to current methods of H 2 O 2 production. N -Hydroxyphthalimide (NHPI) catalyzed low-temperature photochemical aerobic oxidation of benzylic alcohols with no metal co-catalysts allow both the oxidized products and H 2 O 2 to be isolated.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc04351c